I’m excited to revisit this conversation with Annie Duke to the show to talk about her book, How to Decide: Simple Tools for Making Better Choices. Annie is a former professional poker player turned decision strategist who blends cognitive psychology, high-stakes poker, and practical frameworks to help us make better choices in work and life—even when we don’t have all the information.

In this conversation, we cover:

Luck, Skill, and Outcomes: Annie explains why we need to stop judging our decisions solely by outcomes—and how separating luck from skill leads to better learning and better choices over time.
Thinking in Bets and Living with Uncertainty: Drawing from her poker career and academic background, Annie shows how “thinking in bets” helps us navigate uncertainty, manage risk, and make sound decisions even when the long run is a long way off.
Simple Decision Tools and Knowledge Tracking: We talk about practical decision processes—like writing down what you knew, what you believed, and what you predicted at the time—to close feedback loops faster and improve your judgment without needing 10,000 repetitions.
Escaping Bias, Sunk Costs, and Identity Traps: Annie unpacks how status quo bias, sunk cost fallacy, and “identity-protective cognition” keep us defending past choices instead of seeking truth—and how a better decision process helps us see options more objectively.
Confidence, Quitting, and Knowing When to Pivot: We explore how to calibrate confidence, tell the difference between a mountain and a molehill, and decide when perseverance serves you—and when it’s wiser (and more productive) to climb back down and choose a different path.

Annie’s insights take decision-making out of the realm of “go with your gut” and into a practical, repeatable process you can use for everything from small daily choices to major career moves. If you’ve ever looked back and thought, “If I knew then what I know now…”, this episode will give you tools to reduce those regrets and make more confident, informed decisions going forward.

Learn more about Annie and her work at AnnieDuke.com, where you’ll find her books, talks, and newsletter, along with ways to connect further. You can also find How to Decide wherever books are sold.

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Annie Duke on Better Decisions: How to Decide at Work and Life